Mentor Monday: Learning the Hard Way So You Don’t Have To

Disclaimer: The ideas shared in this post are a synthesis of lessons from mentors, insights from peers, and my own personal reflections. They represent an effort to unify the valuable teachings I’ve received throughout my professional and personal journey. While not all concepts are original to me, I’ve gathered and presented them here as a collection of the wisdom, guidance, and “golden nuggets” I’ve absorbed from others.

The Bigger the Boat, the Slower the Movement

One of the most significant lessons I have learned in leadership, organizational life, and systems work is that the bigger the boat, the slower the movement. When you are a passenger, you see only your corner of the ship. You look around and naturally wonder why progress feels delayed or inconsistent. You may ask yourself why the ship is not moving, why things feel stuck, or what you personally can do to influence the direction. These questions are not just common; they are central to understanding systems change and the discomfort that so often accompanies it.

Understanding Organizations as Boats

Organizations function much like large vessels. They are shaped by two core components: culture and systems. Culture consists of the shared values, beliefs, traditions, and informal norms that guide how people interact. Systems consist of the structures, processes, policies, and decision-making pathways that facilitate how work gets done.

Passengers experience culture first. They feel the atmosphere, the communication style, the morale, and the interpersonal dynamics. Systems, however, determine movement, direction, and action. Culture influences how people feel on deck. Systems determine whether the ship can actually leave the dock.

Because passengers primarily see what occurs on the surface, it is easy to misunderstand the complexity beneath. You may see a stalled boat and assume someone simply needs to push a button, when in reality entire teams are coordinating repairs, approvals, and safety protocols you cannot see

Why Change Feels Slow in Large Systems

Large systems require layers of coordination. A small example illustrates this well. If a cruise ship passenger reports a broken toilet, the solution seems simple from the outside. In practice, a maintenance worker must be available, a work order must be approved, parts must be accessible, and safety protocols must be followed. The crew may also be responding to higher priority issues affecting other cabins.

This dynamic mirrors organizational change. What appears to be a simple fix often involves numerous individuals, multiple steps, and competing priorities. Even if everyone wants to help, the structure itself introduces delays. This is not an issue of care or commitment. It is the nature of complex systems.

Fighting for a Sunrise You May Never See

Advocacy and leadership often require accepting that the outcomes of your efforts may not materialize until after you have left the environment where you invested your time. The fact that you may never see the final impact does not invalidate your contribution. Real systems change is cumulative and rarely immediate. You may be planting seeds others will water, nurture, and ultimately see bloom. This is not failure. It is the reality of working within long-standing structures.

Problems, Symptoms, and the Game of Telephone

A common challenge in organizational settings is the distinction between problems and symptoms. Many concerns that are reported represent surface-level expressions of deeper issues. As the concern travels from one person to another, crucial details may be lost or altered. By the time the issue reaches someone who can address it, the information may be incomplete, unclear, or entirely reframed.

This phenomenon creates a significant barrier to meaningful solutions. Without accurate, detailed, and comprehensive descriptions of the root issue, leaders are left responding only to fragments of the problem rather than its full context. As a result, progress slows and the organization’s capacity to respond effectively becomes limited. High-functioning systems strive for second-order change, which focuses on addressing the underlying causes rather than simply managing the immediate symptoms. When organizations operate only at the level of first-order change, they remain trapped in a cycle of putting out fires. When organizations pursue second-order change, they move toward long-term stability, fewer recurring crises, and more sustainable progress for everyone involved. However, this level of change is inherently slow, often requiring patience, persistence, and a willingness to tolerate discomfort while deeper structural shifts take place.

How Large Systems Prioritize Issues

Large systems face constant challenges and must prioritize based on urgency, safety, and scale. A small inconvenience that affects one person cannot outweigh a systems-level issue that impacts many. On a cruise ship, a broken ice cream machine is frustrating, but a mechanical failure that affects navigation is an emergency. Likewise, within organizations, small complaints often cannot be addressed until major structural barriers are resolved.

The bigger the ship, the less individualized the service. It can feel as though your concerns are minimized, but often the system is contending with broader issues that must be addressed before more specific problems can be resolved.

The Challenge of Passive Complaining

Another reality in leadership is that many individuals are more likely to complain publicly than participate meaningfully in change efforts. Some may express frustration on social media but choose not to complete a survey or contribute data that leaders need in order to understand the problem. They occupy the role of sideline critics rather than active contributors. This pattern appears in student organizations, agencies, nonprofits, and school systems. As leaders, it is important not to internalize this dynamic or interpret it as a personal failure. Leaders can only work with the information and engagement that is offered.

What You Can Control as a Passenger or Leader

Individuals have more agency than they often realize, even within slow-moving systems. You can gather accurate information, identify root causes, encourage others to participate constructively, and maintain clarity about what is within your influence. You can advocate for improvements, contribute to healthier culture, and support transparency. You can also refrain from internalizing every criticism, recognizing that not all concerns are a reflection of your leadership. Finally, you can recognize when a particular ship may not be able to take you where you hope to go. There is courage in both staying and leaving. What matters most is aligning your efforts with your values and maintaining realistic expectations.

Conclusion

Navigating large systems requires patience, grounded expectations, and a willingness to understand the complexity behind what appears stagnant on the surface. Slow movement is still movement. You are responsible for the integrity of your role, your willingness to advocate for meaningful change, and the way you show up during periods of uncertainty.

Even when the horizon seems distant, your work contributes to the conditions that make progress possible. You may not see the sunrise, but your efforts help ensure that it will come.